Ruberythric acid

Details

• Internal ID: feea33ba-bfa6-4d9d-9fd5-8ed0cd50787e
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-9,10-dione
• SMILES (Canonical): C1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(C4=C(C=C3)C(=O)C5=CC=CC=C5C4=O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C4=C(C=C3)C(=O)C5=CC=CC=C5C4=O)O)O)O)O)O)O)O
• InChI: InChI=1S/C25H26O13/c26-12-7-35-24(22(33)18(12)29)36-8-14-20(31)21(32)23(34)25(38-14)37-13-6-5-11-15(19(13)30)17(28)10-4-2-1-3-9(10)16(11)27/h1-6,12,14,18,20-26,29-34H,7-8H2/t12-,14-,18+,20-,21+,22-,23-,24+,25-/m1/s1
• InChI Key: GCGGSVAWTYHZBI-CVQRFVFPSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₁₃
• Molecular Weight: 534.50 g/mol
• Exact Mass: 534.13734088 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.19
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• 152-84-1
• Rubianic acid
• Alizarin primeveroside
• Rubierythric acid
• CCRIS 4531
• EINECS 205-808-9
• BRN 0071586
• UNII-4360A2Y7JD
• 1-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-9,10-dione
• 4360A2Y7JD
• beta-D-1-Hydroxy-2-anthraquinonyl 6-O-beta-D-xylopyranosylglucopyranoside
• 1-Hydroxy-2-((6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy)anthraquinone
• 1-Hydroxy-2-[(6-o-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]anthraquinone
• Glucopyranoside, 1-hydroxy-2-anthraquinonyl 6-O-beta-D-xylopyranosyl-, beta-D-
• 1-Hydroxy-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)anthracene-9,10-dione
• RUBIAN
• RUBERYTHRINIC ACID
• RUBERYTHRIC ACID [MI]
• SCHEMBL2135802
• DTXSID701026553
• C25H26O13
• AKOS040735719
• LS-71486
• Q733425
• Ruberythric acid (Alizarin-2-beta-D-primeveroside)
• 1-hydroxy-2-anthraquinonyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside
• 1-Hydroxy-2-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-9,10-anthracenedione
• 1-HYDROXY-2-ANTHRAQUINONYL 6-O-.BETA.-D-XYLOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE
• 9,10-Anthracenedione, 1-hydroxy-2-((6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6687	66.87%
Caco-2	-	0.9265	92.65%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5129	51.29%
OATP2B1 inhibitior	-	0.5626	56.26%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9390	93.90%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6489	64.89%
P-glycoprotein inhibitior	-	0.7025	70.25%
P-glycoprotein substrate	-	0.6684	66.84%
CYP3A4 substrate	+	0.6164	61.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8483	84.83%
CYP3A4 inhibition	-	0.9066	90.66%
CYP2C9 inhibition	-	0.9505	95.05%
CYP2C19 inhibition	-	0.9020	90.20%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	-	0.9063	90.63%
CYP2C8 inhibition	-	0.6235	62.35%
CYP inhibitory promiscuity	-	0.9639	96.39%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6866	68.66%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8969	89.69%
Skin irritation	-	0.8485	84.85%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	+	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4602	46.02%
Micronuclear	+	0.5574	55.74%
Hepatotoxicity	-	0.7328	73.28%
skin sensitisation	-	0.8841	88.41%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7851	78.51%
Acute Oral Toxicity (c)	III	0.4977	49.77%
Estrogen receptor binding	+	0.7522	75.22%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.4949	49.49%
Glucocorticoid receptor binding	-	0.5629	56.29%
Aromatase binding	+	0.6613	66.13%
PPAR gamma	+	0.7765	77.65%
Honey bee toxicity	-	0.7743	77.43%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7149	71.49%
Fish aquatic toxicity	+	0.9052	90.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.20%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.15%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.98%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.61%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	91.87%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.17%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.95%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.86%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.94%	95.83%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.41%	89.62%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.31%	96.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.08%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.89%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	83.37%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.47%	99.23%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.53%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.34%	96.00%

Plants that contains it

• Rubia argyi
• Rubia cordifolia
• Rubia tinctorum

Cross-Links

• PubChem: 92101
• NPASS: NPC87857
• LOTUS: LTS0171846
• wikiData: Q733425